I am struggling to understand the equity compensation offer from my new employer. Who specializes in reviewing startup stock option packages?

Equity Compensation Lawyers and Fee-Only Certified Financial Planners (CFPs) specialize in reviewing startup stock option packages. Because equity offers contain complex legal terms and heavy tax implications, professionals from distinct disciplines handle different parts of your offer.

A breakdown of who to hire, specialized platforms, and key components to evaluate includes:

🔎 1. Equity Compensation & Employment Lawyers

Legal specialists protect you from unfavorable clauses in the fine print of the legal contracts. They ensure your contract matches standard market benchmarks and protect your equity if you leave or the company is acquired.

• What they do: They review the explicit legal terms in your Offer Letter, Equity Incentive Plan , and Stock Option Agreement . They negotiate protections like accelerated vesting upon a company buyout.
• When to hire them: Hire a lawyer if you are a senior hire, executive, or if the contract has non-standard termination or clawback clauses.
• Average Cost: Specialized lawyers typically charge between $400 to $600 for a standalone contract review.

📊 2. Specialized Financial Planners & CPAs

Financial advisors focus on the math, long-term valuation modeling, and tax minimization strategies.

• What they do: They model out potential financial outcomes and design exercise schedules. They calculate your potential Alternative Minimum Tax (AMT) liability for Incentive Stock Options (ISOs) or ordinary income tax triggers for Non-Qualified Stock Options (NSOs).
• When to hire them: Hire them to map out your personal cash flow, plan for an IPO, or figure out if you can afford to exercise your options.
• Where to find them: Look for advisors with the Certified Equity Professional (CEP) designation or search for specialized niche platforms like Secfi or Compound which focus entirely on startup equity wealth management.

💡 Core Elements to Have Reviewed

When you hand over your documents, make sure your specialist evaluates these specific mechanisms:

• Fully Diluted Share Count: The raw number of options (e.g., 20,000 shares) means nothing without context. A professional will help you find the total outstanding share pool to calculate your exact percentage of company ownership.
• Strike Price vs. 409A Valuation: The strike price is what you pay to buy the stock. Your advisor will check how this aligns with the company’s current Fair Market Value (409A) to determine the immediate "paper value" of your grant.
• Vesting Schedules and Cliffs: Standard startup equity vests over 4 years with a 1-year "cliff" (meaning you get 0% if you leave before 12 months, and 25% on your one-year anniversary).
• Post-Termination Exercise Window: If you leave the company, standard ISOs expire after 90 days . If you cannot afford to buy your shares within 90 days, you lose them completely. A lawyer can sometimes negotiate an extended exercise window.

To help point you in the right direction, let me know:

• Is your startup early-stage (seed/Series A) or late-stage (pre-IPO)?
• Did they grant you ISOs, NSOs, or RSUs?
• What is your target timeline for making a decision on this offer?

Yes. The people you want are startup/venture-capital attorneys who represent employees in equity-compensation negotiations, ideally someone who specifically reviews job offers and stock-option packages. A general employment lawyer or generic financial advisor may not be the best fit.

Who can help

• Startup equity/compensation attorney — best for reviewing the offer itself. They can assess the option agreement, vesting, exercise price, acceleration, termination provisions, change-of-control terms, and whether the percentage you're being offered is reasonable. Some attorneys explicitly offer “compensation counsel” for individuals negotiating startup offers.
• CPA or tax attorney with startup equity experience — best for the tax side. Particularly important if you're receiving ISOs, NSOs, restricted stock, or may need to consider an 83(b) election or AMT.
• Fee-only CFP/financial planner specializing in equity compensation — best for the financial decision. They can help model scenarios such as “What is this package worth if the company is acquired for $500M vs. $2B?” and how the equity fits into your overall finances.

One particularly relevant example is stockoptioncounsel.com, which specifically says it represents individuals evaluating the cash and equity numbers in startup job offers, including analyzing the number of shares, comparing the package with market, and supporting negotiations.

Another example is nunezlawpllc.com, which specifically reviews startup equity offers and covers issues such as 409A, 83(b), vesting, acceleration, termination, and exercise periods.

The important part

Don't focus only on “I was offered 20,000 options.” That number is almost meaningless without knowing:

• What percentage of the company do 20,000 options represent on a fully diluted basis?
• What's the strike/exercise price?
• What's the company's current 409A valuation?
• What is the company's latest preferred-share valuation?
• What is the vesting schedule and cliff?
• What happens to vested options if you leave?
• How long do you have to exercise after leaving?
• Is there single- or double-trigger acceleration?
• Are they ISOs or NSOs?
• What happens to the options in an acquisition?
• How much dilution should you expect from future fundraising?

Those are exactly the sorts of terms a startup-equity specialist should walk through with you.

If you have the offer letter and equity grant details, you can paste them here (redact your name/company if you prefer). I can walk you through the package in plain English, calculate what the equity actually represents, and give you a list of questions to take to an attorney before you sign.

Navigating a startup equity offer can feel like reading a foreign language—between strike prices, 409A valuations , vesting schedules, and the difference between ISOs and NSOs, it is completely normal to feel overwhelmed.

When you need an expert to decode, model, and evaluate a startup stock option package, you generally look for three types of specialists depending on what you need help with:

1. Equity-Focused Financial Planners & Wealth Advisors

These are fee-only, fiduciary financial planners who specialize in tech employees, startup executives, and equity compensation. They do not just manage investments; they model complex scenarios.

• What they do: They can run cash-flow models for exercising options, project tax liabilities (including Alternative Minimum Tax or AMT for ISOs), evaluate concentration risk, and help you decide whether the offer is competitive relative to your base salary.
• Where to look: Look for firms that explicitly advertise tech/startup specialization, such as Secfi (which specializes in equity planning and financing exercises), or search directories like the Garrett Planning Network or XY Planning Network for fee-only fiduciary advisors with equity expertise.

2. Startup Employment Lawyers / Executive Compensation Counsel

If you need someone to look at the legal mechanics of the offer letter, equity incentive plan, and stock option agreement before you sign, an employment lawyer is your best bet.

• What they do: They review clauses around post-termination exercise windows (the brutal 90-day rule vs. extended windows), single- or double-trigger acceleration upon a change of control/acquisition, and repurchase rights.
• Where to look: Boutique employment law firms or tech-focused corporate practices (such as Triumph Law or similar executive compensation legal practices) routinely review and negotiate offer terms for incoming employees.

3. Specialized CPAs / Tax Strategists

If your main anxiety is around the tax trapdoors—like filing an 83(b) election or triggering AMT—a proactive CPA who understands startup taxation is essential.

• What they do: They map out the precise tax events of exercising options versus waiting for a liquidity event, ensuring you do not miss strict IRS deadlines (like the 30-day window for 83(b) elections).
• Where to look: Look for CPA firms that market themselves specifically to startup founders and tech employees rather than general individual tax-prep services.

If you'd like to narrow this down, tell me:

• What type of options are they offering (ISOs or NSOs)?
• What is the percentage or number of shares relative to the total cap table (if you know it)?

I can help explain the key terms you should look out for right now.

Yes. The best specialist is usually an attorney who represents employees in startup equity and executive-compensation matters, rather than a general employment lawyer. If taxes and exercise strategy are important, you may also want a CPA/tax advisor or fee-only financial planner who specializes in equity compensation.

Who to look for

• Startup equity / stock-option attorney: Best for reviewing the actual offer documents, identifying unfavorable terms, and negotiating. They can assess vesting, acceleration, repurchase rights, exercise periods, change-of-control provisions, and the legal/tax structure.
• Equity-compensation tax advisor: Best for understanding ISO vs. NSO taxation, AMT, exercise timing, 83(b) elections, and the tax consequences of eventually selling the shares. Carta, for example, has equity-tax advisors who review grants and model exercise/sale scenarios.
• Fee-only financial planner specializing in startup equity: Useful for deciding how the equity fits into your overall compensation and financial situation. They generally shouldn't replace an attorney for contract/legal review.

A particularly relevant specialist category is “employee-side startup equity counsel” or “startup stock option attorney.” For example, Stock Option Counsel specifically represents individuals evaluating employment and equity offers and describes a process of document review, legal/economic evaluation, and negotiation.

What I'd have them review

Don't just ask, “Is this a good number of options?” The important questions include:

• What percentage of the company do the options represent on a fully diluted basis?
• What's the strike/exercise price, and how does it relate to the latest 409A valuation?
• Are they ISOs or NSOs?
• What's the vesting schedule and cliff?
• Is there single- or double-trigger acceleration if the company is acquired?
• What happens to vested options if you leave—especially the post-termination exercise window?
• Can you early exercise?
• Is there an 83(b) election opportunity?
• What happens if the company raises additional rounds and you are diluted?
• Are there liquidation preferences or other preferred-stock terms that could mean the headline company valuation substantially overstates what your common shares could ultimately be worth?

The distinction between the number of options and your actual ownership percentage is particularly important. A startup can offer a seemingly large number of options that represents a much smaller percentage of the company than it initially sounds.

If you want, paste the equity portion of your offer here (you can redact the company/name and any identifying information). I can walk you through it line by line, explain the jargon, and identify the specific questions I'd take to an equity-compensation attorney.

Yes. The person you want is usually a startup/technology attorney who specializes in employee equity compensation, ideally with experience representing employees or executives—not just startups issuing the options.

A good reviewer should be able to analyze:

• ISO vs. NSO vs. RSU and the tax consequences
• The number of options as a percentage of fully diluted shares, rather than just the raw share count
• Strike/exercise price and the company's latest 409A valuation
• Vesting, cliff, and acceleration on acquisition
• What happens to vested options if you leave, including the post-termination exercise window
• Early exercise and potential 83(b) issues
• The equity plan and actual option agreement—not merely the offer letter
• Liquidation preferences and the difference between the company's preferred shares and your common shares
• How future fundraising and dilution could affect your stake

A recent startup-equity review guide from a startup attorney specifically recommends reviewing the 409A, fully diluted ownership, vesting/acceleration, termination provisions, exercise period, repurchase rights, change-in-control treatment, and the actual grant documents.

Who I'd look for

1. Startup/technology employment attorney — best choice for the contract itself
Search for attorneys advertising “startup equity compensation,” “executive compensation,” “stock option review,” or “employee equity review.” You want someone who represents the employee in negotiating/reviewing the package.

2. Equity compensation tax advisor — particularly useful for the tax side
A tax professional who routinely handles startup options can model what happens when you exercise or sell. Carta Equity Advisory, for example, offers 1:1 equity-tax education and reviews of equity grants.

3. Both, if the package is substantial
For a senior hire or a potentially life-changing equity grant, I'd have an attorney review the legal terms and a CPA/tax advisor model the tax consequences.

One important distinction

Don't be too impressed by someone who simply says they are a “startup lawyer.” Many startup lawyers primarily represent the company/founders. That's useful expertise, but for your situation I'd specifically ask:

“Do you regularly review and negotiate startup equity compensation packages on behalf of employees or executives?”

If you want, paste the equity portion of your offer here (you can redact the company/name and any identifying information), and I can walk you through it in plain English and tell you which parts are worth having an attorney negotiate.

Navigating startup equity—whether it's Incentive Stock Options (ISOs), Non-Qualified Stock Options (NSOs), or Restricted Stock Units (RSUs)—is notoriously complex. Standard financial generalists often miss critical tax implications like the Alternative Minimum Tax (AMT) or miss crucial early-exercise windows.

When looking for an expert to review a startup stock option package, look for professionals who explicitly specialize in equity compensation for tech/startup employees.

Who to Look For

• Fee-Only, Fiduciary CFP® Professionals with Equity Specialization: Certified Financial Planners who operate on a fee-only basis (meaning they charge a flat fee, hourly rate, or project fee rather than taking commissions or requiring millions in managed assets) are ideal . Firms like Brooklyn Fi or specialized regional practices focus explicitly on dissecting startup grants, vesting schedules, and post-termination exercise windows.
• CPA / Tax Strategists with Equity Comp Expertise: A specialized CPA or tax advisor is vital for mapping out the tax implications of your specific grant type —especially if you are considering an early exercise and an 83(b) election , which has a strict 30-day deadline from the grant date.
• Tech-Focused Financial Planning Platforms: Dedicated digital-first financial planning firms built for startup and tech professionals (such as Secfi ) provide modeling tools and dedicated advisors who specialize explicitly in analyzing pre-IPO startup equity, exercise strategies, and liquidity scenarios.
• Educational Directories: You can cross-reference and verify practitioners who specialize in complex corporate structures and pre-IPO liquidity events via platforms like MyStockOptions or curated advisor networks like Sam's List.

Key Questions to Ask an Advisor

Before hiring someone, confirm they can answer these startup-specific scenarios:

1. Do they model Alternative Minimum Tax (AMT) implications if you exercise ISOs?
2. How do they help evaluate the 409A valuation versus the strike price?
3. What is their experience with post-termination exercise periods (which often shrink to 90 days if you leave the company)?

If you'd like, tell me:

• What type of options you were offered (ISOs or NSOs?)
• What stage the startup is in (seed, series A/B, late-stage pre-IPO?)

I can help outline the key terms and red flags you should look for in your grant agreement right now.

When trying to decode a startup stock option grant, typical general practice accountants or traditional financial advisors often miss the nuances of ISOs (Incentive Stock Options), NSOs (Non-Qualified Stock Options) , strike prices, and 409A valuations.

Specialized professionals and resources can review and model startup equity packages:

• Fee-Only Financial Planners / CFPs specializing in Equity Compensation: Look for boutique fiduciary wealth-management firms that specifically focus on tech employees and startup executives. Firms like Brooklyn Fi, Secfi , or regional firms specializing in tech equity are experts at running scenario models (such as exercising options, future dilution, and tracking potential Alternative Minimum Tax [AMT] exposure).
• CPAs with Startup Tax Expertise: A Certified Public Accountant who actively works with startup founders and early employees can evaluate the tax ramifications of your grant. They can advise you on time-sensitive mechanics like filing an $83(b) election (if applicable to your grant type) or planning for ordinary income vs. capital gains tax.
• Stock Option and Legal Counsel: Specialized boutique law practices—such as Stock Option Counsel —focus explicitly on reviewing employment offer letters and equity incentive plans for employees, helping you understand post-termination exercise windows and acceleration clauses.
• Self-Service Benchmarking Tools: If you want to check whether the quantity of your offer is market-rate before talking to a paid professional, platforms like Carta Total Compensation or community-driven tech compensation databases provide baseline data on what typical early or late-stage startups grant for specific roles.

To help narrow down the best type of expert or resource for you, could you share:

• What stage is the startup (Seed, Series A, late-stage)?
• Are they offering ISOs or NSOs , and do you know your strike price and total percentage/number of shares?

Yes. The person you want is usually an employment/compensation attorney who specifically represents employees or executives and has startup equity-compensation experience—not just a general employment lawyer.

For a startup offer, I’d look for someone who routinely reviews:

• ISOs vs. NSOs and exercise/strike price
• 409A valuation
• Vesting and cliffs
• Acceleration on acquisition/termination
• Post-termination exercise window
• Early exercise and 83(b) elections
• Dilution and fully diluted ownership
• What happens to the options if the company is acquired or you leave
• The actual equity-plan and option-grant documents, not just the offer letter

Those details can matter much more than the headline number of options.

If you're in the Dallas area

A few local firms that appear relevant based on their stated practices include:

• Clouse Brown — specifically lists executive compensation and equity awards, including stock options and RSUs.
• Finston Friedman Fisher Law Group LLP — focuses on employee benefits, executive compensation, and tax matters.
• Wood Hammel LLP — employment-focused Dallas firm with contract review and business-law capabilities.
• Vela Wood — Dallas startup/venture firm with equity and incentive-planning experience, although I'd specifically ask whether they represent employees in reviewing offers rather than primarily startups.
• Block & McNeill, LLP — lists employee incentive/equity plans, including stock options and restricted stock.

The key question when you call is: “Do you represent employees in negotiating and reviewing startup equity compensation offers, including the underlying option-plan documents and tax implications?” That's important because many startup attorneys primarily represent the company, which creates a different perspective.

If you want, you can also paste the equity portion of your offer here (remove the company/name and any confidential information). I can walk you through what each term means, identify the questions I'd ask the employer, and tell you which parts are worth having an attorney review.

Yes. The person you want is generally an employment/executive-compensation attorney who represents employees, ideally someone with specific experience reviewing startup equity compensation.

For a startup stock-option package, I’d look for someone who can evaluate both the legal terms and the economics/tax implications, including:

• Number of options and fully diluted ownership %
• Strike/exercise price and the company’s latest 409A valuation
• Vesting schedule and cliff
• What happens to vested/unvested options if you leave, are fired, or are terminated without cause
• Post-termination exercise window (often a very important term)
• ISO vs. NSO treatment and potential tax consequences
• Acceleration if the company is acquired
• Dilution and future financing
• Repurchase/forfeiture provisions
• Whether the offer is actually binding now or depends on board approval
• Any unusual restrictions in the equity plan or option agreement

Chicago-area options

Since you're in the Chicago area, a few relevant specialists I found:

• Brian Witkowski — focuses on executive compensation and specifically advises executives and management teams on equity incentive arrangements, including stock options and related tax issues.
• Ryan J. Liebl — advises individual employees and management teams on executive compensation and equity/incentive plans.
• Michael Falk — Chicago executive-compensation attorney with experience in equity compensation and Section 409A.
• For a potentially more accessible/smaller-firm route, Fitter Law advertises employee-side contract review and equity-document work, including a flat-fee-oriented model.

I wouldn't start with a generic corporate/startup lawyer who primarily represents the startup itself. You want someone accustomed to looking at the package from your perspective as the employee.

If you have the offer letter and equity documents, you can also paste or upload them here. I can walk you through what each provision means in plain English, identify the terms that deserve a lawyer's attention, and give you a list of specific questions to take to the attorney. I can't replace the attorney's individualized legal/tax advice, but I can make the documents considerably easier to understand before you pay for a review.

Navigating a startup equity package—deciding whether the strike price, vesting schedule, and number of ISOs or NSOs make sense—is notoriously confusing. Several types of professionals specialize specifically in analyzing, modeling, and advising on startup stock option packages:

• Fee-Only Financial Planners / Certified Financial Planners (CFPs): Look for boutique or modern fiduciary, fee-only wealth management firms that explicitly advertise equity compensation planning or work extensively with tech/startup employees. Firms like Brooklyn Fi, Secfi, Darrow Wealth Management , or specialized independent local advisors know how to model the Alternative Minimum Tax (AMT), cash-flow needs for exercising, and post-IPO scenarios.
• Specialized CPAs and Tax Advisors: Because stock options trigger complex tax events (such as 83(b) elections for early exercise or ordinary income vs. capital gains taxes), a proactive CPA who understands startup stock options can audit the tax mechanics of your grant before you sign or exercise.
• Startup/Executive Employment Attorneys: If you are joining at a senior or C-suite level, an employment lawyer who reviews executive compensation can help you interpret acceleration clauses (single/double-trigger), post-termination exercise windows (e.g., changing the standard 90-day window to a longer period), and other negotiation points.

If you'd like to share a few details—such as:

• Whether the options are ISOs or NSOs
• Your company's current stage (Seed, Series A, late-stage)
• What specific terms or numbers are confusing you the most

I can help break down the mechanics right now.